N-Boc-4,4-difluoro-L-proline

CAS Number 203866-15-3

Fluorinated Building Blocks, Heterocyclic Building Blocks, Monomers

N-Boc-4,4-difluoro-L-proline CAS 203866-15-3

A difluorinated l-proline derivative

Used as a molecular scaffold for biochemistry and a conformational tool for polypeptides

Overview
Related Products

N-Boc-4,4-difluoro-l-proline (CAS number 203866-15-3) is a tert-butoxycarbonyl (Boc) protected l-proline with two fluorine substituents at 4-position. N-Boc-4,4-difluoro-l-proline is an S-enantiomer, making it an excellent additive/catalyst in asymmetric reactions. In protein/peptide chemistry, N-Boc-4,4-difluoro-l-proline is introduced for conformational control favouring 78% cis-conformers. The conformation selectivity is also expressed in the ¹⁹F NMR spectrum which is a powerful tool to study the isomerisation of peptides and proteins.

N-Boc-4,4-difluoro-l-proline is also applied as a molecular scaffold for synthesising fibroblast activation protein, a trans-membrane serine protease.

Multiple functional groups

For facile synthesis

Fluorinated l-proline building block

For organic synthesis, medicinal chemistry and biochemistry research

Worldwide shipping

Quick and reliable shipping

High purity

>97% High purity

General Information

CAS Number	203866-15-3
Chemical Formula	C₁₀H₁₅F₂NO₄
Full Name	(S)-1-(tert-Butoxycarbonyl)-4,4-difluoro-2-pyrrolidinecarboxylic acid
Molecular Weight	251.23 g/mol
Synonyms	N-(tert-Butoxycarbonyl)-4,4-difluoro-l-proline
Classification / Family	Fluorinated building blocks, Heterocyclic building blocks, Proteins, Peptides, Asymmetric synthesis, Chiral molecules

Chemical Structure

Product Details

Purity	97%
Melting Point	T_m = 120 °C – 140 °C
Optical Rotation	−44.19 ° (c = 1, methanol)
Appearance	Off-white powder

MSDS Documentation

N-Boc-4,4-difluoro-l-proline MSDS Sheet

Literature and Reviews

Deciphering the fluorine code—the many hats fluorine wears in a protein environment, A. Berger et al., Acc. Chem. Res., 2017, 50, 2093–2103(2017); DOI: 10.1021/acs.accounts.7b00226.
Minimising conformational bias in fluoroprolines through vicinal difluorination, G.-J. Hofman et al., Chem. Commun., 54, 5118(2018); DOI: 10.1039/c8cc01493k.
Fluorinated prolines as conformational tools and reporters for peptide and protein chemistry, S. Verhoork et al., Biochemistry, 57(43), 6132–6143(2018); DOI: 10.1021/acs.biochem.8b00787.
Novel small molecule-derived, highly selective substrates for fibroblast activation protein (FAP), A. De Decker et al., ACS Med. Chem. Lett., 10, 1173–1179(2019); DOI: 10.1021/acsmedchemlett.9b00191.

Related Products

We stock a wide range of monomer available to purchase online. Please contact us if you cannot find what you are looking for.

Potassium nonafluoro-1-butanesulfonate

From £50

2-Fluorobiphenyl

From £40

Pentafluorobenzoic acid

From £30

2,4,5-Trifluorophenylacetic acid

From £40

4-Fluoro-1,2-phenylenediamine

From £35

5-Fluorobenzoxazole-2-thiol

From £45

5-Bromo-3-fluoropyridine-2-carboxylic acid

From £55

7-Fluoro-4-hydroxycoumarin

From £50

2-Amino-5-chloro-3-fluoropyridine

From £40

5-Fluoro-2-methylbenzoic acid

From £45

5-Bromo-4-fluoro-2-methylaniline

From £60

3′-Bromo-4′-fluoroacetophenone

From £35

3-Fluoro-5-(trifluoromethyl)benzoic acid

From £30

5-Chloro-2-fluorobenzonitrile

From £40

2-Fluoro-6-methylbenzoic acid

From £33

4′-Fluoro-3′-nitroacetophenone

From £35

4-Fluoro-3-methylbenzoic acid

From £50

1,3,5-Tris(3-fluoro-4-formylphenyl)benzene

£80
From £80

5-Chloro-2-fluorobenzoic acid

From £50

2-Fluoro-5-methylbenzoic acid

From £50

trans-3,4-Difluorocinnamic acid

From £50

4-Fluoro-2-iodobenzoic acid

From £35

3-Fluoro-4-iodopyridine

From £50

2-Chloro-5-fluoronitrobenzene

From £45

4-Bromo-3-fluorobenzonitrile

From £50

3-Bromo-5-fluorophenol

From £33

4-Bromo-3-fluoroiodobenzene

From £35

5-Difluoromethoxy-2-mercaptobenzimidazole

From £65

6-Fluoro-4-hydroxy-2-(trifluoromethyl)quinoline

From £95

4-Bromo-6-fluoroquinoline

From £95

4-Amino-2-(trifluoromethyl)pyridine

From £50

1-(3-Fluorophenyl)-1H-pyrazole-4-carbaldehyde

From £70

Methyl 6-fluoropyridine-2-carboxylate

From £85

4-Hydroxy-2-(trifluoromethyl)benzoic acid

From £65

5-Bromo-2-fluoropyrimidine

From £60

3-Chloro-5-fluoroaniline

From £65

6-Fluoropyridine-2-carbonitrile

From £80

4-Fluoro-4′-methoxybenzophenone

From £90

2,4,6-Trifluorophenylacetic acid

From £90

2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid

From £80

2-Fluoropyridine-3-carbonitrile

From £90

2-Bromo-5-fluorobenzonitrile

From £60

1-Bromo-2-chloro-4-fluorobenzene

From £70

2-Fluoro-4-(trifluoromethyl)benzoic acid

From £100

3-Fluoro-4-methoxybenzoic acid

From £90

4-Methoxy-3-(trifluoromethyl)aniline

From £90

4-Fluoro-2-methylbenzonitrile

From £90

3-Fluoro-4-(trifluoromethyl)benzoic acid

From £90

3,5-Difluoropyridine-2-carbonitrile

From £90

5-Cyano-2-fluoropyridine

From £90

2,6-Difluorocinnamic aldehyde

From £90

2-Fluoro-4-hydroxybenzoic acid

From £90

3-Chloro-2-fluorobenzoic acid

From £75

2-Fluoro-3-methoxybenzaldehyde

From £137

3-Fluorobenzoic hydrazide

From £100

2-Amino-5-fluorobenzonitrile

From £80

4-Fluoro-2-methylphenol

From £60

2,4,5-Trifluorobenzonitrile

From £80

4-Chloro-3-fluoroaniline

From £50

2-Fluoro-4-nitroaniline

From £70

3-Fluoro-2-methylbenzoic acid

From £90

2-Amino-6-fluorobenzonitrile

From £90

3-Fluoro-p-anisidine

From £90

3′-Fluoro-4′-methoxyacetophenone

Price £90

2-Bromo-4-fluorobenzonitrile

From £80

3-Fluoro-2-pyridinecarbonitrile

From £70

2-Amino-3-fluoropyridine

From £80

3-Fluoro-4-hydroxybenzaldehyde

From £80

α,α-Difluorophenylacetic acid

From £70

3,3-Difluoropiperidine hydrochloride

From £60

2,2-Difluorocyclopropanecarboxylic acid

From £90

4-Fluoro-β-nitrostyrene

From £90

2,6-Dichloro-5-fluoro-3-pyridinecarbonitrile

From £90

2-Fluoro-4-(trifluoromethyl)aniline

From £90

3,4,5-Trifluorobenzoic acid

From £90

2-Bromo-3′-fluoroacetophenone

From £116

4-Fluororesorcinol

From £70

3,4,5-Trifluoroaniline

From £55

4-Fluorobenzenesulfonamide

From £65

2-Fluoro-5-nitrobenzoic acid

From £65

1-Bis(4-fluorophenyl)methyl piperazine

From £80

3,5-Difluorobenzonitrile

From £65

6-Fluoronicotinic acid

From £76

2-Bromo-4-fluoropyridine

From £125

3-Fluoro-2-hydroxybenzaldehyde

From £110

2-Chloro-5-fluoropyrimidine

From £100

2-Bromo-6-fluorobenzaldehyde

From £100

2-Fluoro-5-nitrobenzonitrile

From £72

Bis(4-fluorophenyl)methanol

From £105

N-Boc-trans-4-fluoro-L-proline

From £76

(S)-(+)-3-Fluoropyrrolidine hydrochloride

From £80

Methyl pentafluorobenzoate

From £76

5-Fluorosalicylic acid

From £110

(R)-(−)-3-Fluoropyrrolidine hydrochloride

From £72

4-Bromo-2,6-difluoroaniline

From £76

2-Fluoroadenine

From £90

3,3-Difluoropyrrolidine hydrochloride

From £110

4-Fluoro-3-nitrobenzoic acid

From £66

2-Amino-4-fluorophenol

From £56

2,4-Difluorobenzonitrile

From £66

2,4-Difluoro-(1H-1,2,4-triazolyl)acetophenone

From £100

4,4′-Bis(trifluoromethyl)-2,2′-bipyridine

From £100

5-Bromo-2-fluoropyridine

From £105

1-(tert-Butoxycarbonyl)-3-fluoro-4-piperidone

From £90

6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride

From £80

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

From £115

3-Fluoro-4-morpholinoaniline

From £100

Benzyl (3-Fluoro-4-morpholinophenyl)carbamate

From £100

5-Fluoroisatin

From £76

5-Fluorooxindole

From £200

5-(Trifluoromethoxy)isatin

From £115

6-Fluoroindole-2-carboxylic acid

From £105

6-Fluoroindole

From £80

5-Fluoroindole

From £100

7-Fluoroindole

From £170

3-(4-Fluorophenyl)-1-isopropylindole

From £100

4-Fluoroindole

From £100

4-(Trifluoromethyl)-1H-imidazole

From £165

1-[2-(Trifluoromethyl)phenyl]imidazole

From £175

3-(Trifluoromethyl)-2-pyridone

From £100

5-(Trifluoromethyl)-2-pyridone

From £100

2-(Trifluoromethyl)thioxanthen-9-one

Price £95

2-Furoyltrifluoroacetone

From £100

7-(Diethylamino)-4-(trifluoromethyl)coumarin

From £110

7-Hydroxy-4-(trifluoromethyl)coumarin

From £56

2-Fluoro-9H-carbazole

From £135

AB-TFMB

£90
From £90

p-6FDAP

£110
From £110

2,2-Bis(3-(3-aminobenzoylamino)-4-hydroxyphenyl)hexafluoropropane (m-6FDAP)

£130
From £130

2,2'-Bis(trifluoromethyl)-4,4'-diaminodiphenyl ether (6FODA)

£76
From £76

2,2-Bis[4-(4-aminophenoxy)phenyl]hexafluoropropane (4-BDAF)

£76
From £76

1,4-Bis(4-amino-2-trifluoromethylphenoxy)benzene (6FAPB)

£76
From £76

4,4'-(Hexafluoroisopropylidene)diphthalic anhydride (6FDA)

£90
From £90

2,2'-Bis(trifluoromethyl)benzidine (TFMB)

£76
From £76

2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane (6FAP)

£76
From £76

2-(2,4-Difluorophenyl)-5-fluoropyridine

From £105

2-(2,4-Difluorophenyl)-5-methylpyridine

From £130

4-Chloro-7-trifluoromethylquinoline-3-carboxylic acid ethyl ester

From £145

4-Bromo-8-fluoroquinoline

From £135

6-Chloro-8-fluoroquinoline

From £80

8-Fluoro-4-hydroxy-2-methylquinoline

From £95

(5S)-(−)-5-(Trifluoromethyl)-2-pyrrolidinone

From £145

2,4,6-Trifluoronitrobenzene

From £74

Ethyl (4-fluorobenzoyl)acetate

From £110

5-Bromo-3-fluorosalicylaldehyde

From £110

6-Fluoro-4-chromanone

From £120

2-(Difluoromethyl)benzimidazole

From £115

3,3-Difluoroazetidine hydrochloride

Price £170

4-(Trifluoromethyl)-2-pyridone

From £72

4-Fluoro-1H-indazole

From £72

3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

From £115

5,5'-Bis(trifluoromethyl)-2,2'-bipyridine

From £210

5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene

From £250

2-Bromo-6-fluoronaphthalene

From £130

FIC

From £220

HDOQx-DBrDF

From £520

MeHDOQx-DBrDF

From £520

2FIC

From £360

BDTT-F-Sn

From £500

DFBTA-2ThBr-HD

From £310

3,3'-Difluoro-5,5'-bis(trimethylstannyl)-2,2'-bithiophene

From £280

2-Ethylhexyl 4,6-dibromo-3-fluorothieno[3,4-b]thiophene-2-carboxylate

From £260

4,7-Dibromo-5,6-difluoro-2,1,3-benzothiadiazole

From £210

PCE11 Monomer

From £480