4-Nitrobenzyl chloroformate supplier

Name
4-Nitrobenzyl chloroformate
EINECS 224-708-6
CAS No. 4457-32-3
Article Data11
CAS DataBase
Density 1.447 g/cm³
Solubility
Melting Point 32 °C
Formula C₈H₆ClNO₄
Boiling Point 330.8 °C at 760 mmHg
Molecular Weight 215.593
Flash Point 153.8 °C
Transport Information UN 3261 8/PG 2
Appearance off-white to pale yellow powder
Safety 26-36/37/39-45-38-28A-27
Risk Codes 34-37-23/24/25-36/37
Molecular Structure
Hazard Symbols C, T
Synonyms Formicacid, chloro-, p-nitrobenzyl ester (7CI,8CI);4-Nitrobenzyloxycarbonyl chloride;p-Nitrobenzyl chloroformate;p-Nitrobenzyloxycarbonyl chloride;p-Nitrocarbobenzoxy chloride;
PSA 72.12000
LogP 2.99340

Synthetic route

: 75-44-5
phosgene

: 619-73-8
4-nitrobenzyl chloride

: 4457-32-3
4-nitrobenzyl chloroformate

Conditions

Conditions	Yield
In dichloromethane at 20 - 25℃; for 50h;	98%
With chloroform at 60 - 65℃; im geschlossenen Rohr;
With 1,4-dioxane

: 619-73-8
4-nitrobenzyl chloride

: 503-38-8
trichloromethyl chloroformate

: 4457-32-3
4-nitrobenzyl chloroformate

Conditions

Conditions	Yield
With dmap In toluene at 20℃; for 24h;

: 609-36-9
rac-Pro-OH

: 4457-32-3
4-nitrobenzyl chloroformate

: 347386-12-3
1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; Shotten-Baumann reaction;	100%

: 68282-55-3
2-benzyl-1H-imidazole-4-carbaldehyde

: 4457-32-3
4-nitrobenzyl chloroformate

: 623906-05-8
2-benzyl-4-formylimidazole-1-carboxylic acid 4-nitrobenzyl ester

Conditions

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water at 0℃; for 2.5h;	100%
With sodium bicarbonate In 1,4-dioxane; water	100%
With sodium hydrogencarbonate In 1,4-dioxane; water at 0℃; for 2.5h;	100%

: 5625-67-2
2-Ketopiperazine

: 4457-32-3
4-nitrobenzyl chloroformate

: 623564-23-8
4-p-nitrobenzyloxycarbonyl-2-ketopiperazine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane; dichloromethane at 0℃; for 0.5h;	100%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane; dichloromethane at 0℃; for 0.5h;	100%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane; dichloromethane at 0℃; for 0.5h;	100%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane; dichloromethane; water

: 1322746-31-5
(S)-2-tert-butyloxycarbonylamino-4-(piperidin-4-yl)butanoic acid methyl ester

: 4457-32-3
4-nitrobenzyl chloroformate

: 1322746-32-6
(S)-2-tert-butyloxycarbonylamino-4-(1-(4-nitrobenzyloxy)carbonylpiperidin-4-yl)butanoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1.5h; pH=8 - 9;	100%

: C11H17N3O4

: 4457-32-3
4-nitrobenzyl chloroformate

: 8-(tert-butyl) 7-(4-nitrobenzyl) (5S,8S)-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 12h; Inert atmosphere;	100%

: C11H17N3O4

: 4457-32-3
4-nitrobenzyl chloroformate

: 8-(tert-butyl) 7-(4-nitrobenzyl) (5R,8S)-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 12h; Inert atmosphere;	100%

: C11H17N3O4

: 4457-32-3
4-nitrobenzyl chloroformate

: 8-(tert-butyl) 7-(4-nitrobenzyl) (5S,8R)-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 12h; Inert atmosphere;	100%

: C11H17N3O4

: 4457-32-3
4-nitrobenzyl chloroformate

: 8-(tert-butyl) 7-(4-nitrobenzyl) (5R,8R)-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 12h; Inert atmosphere;	100%

: 51-35-4
4R-4-hydroxyproline

: 4457-32-3
4-nitrobenzyl chloroformate

: 96034-57-0
(2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane at 0℃; for 2h; Acylation;	98%
Stage #1: 4R-4-hydroxyproline; 4-nitrobenzyl chloroformate With sodium hydroxide In dichloromethane; water at 0 - 5℃; for 1h; Stage #2: With sulfuric acid In water at 0 - 5℃;	93%
Stage #1: 4R-4-hydroxyproline; 4-nitrobenzyl chloroformate With sodium hydroxide In dichloromethane; water at 0 - 5℃; for 1h; Stage #2: With sulfuric acid In water at 0 - 5℃;	93%

: 62-53-3
aniline

: 4457-32-3
4-nitrobenzyl chloroformate

: 74109-32-3
4-nitrobenzyl phenylcarbamate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 0℃; for 0.25h;	98%

: 4457-32-3
4-nitrobenzyl chloroformate

: 2488-14-4, 149263-87-6
N(α)-tert-butoxycarbonyl-histidine methyl ester

: Boc-His[Z(NO2)]-OMe

Conditions

Conditions	Yield
With triethylamine In chloroform at 0 - 20℃; for 2.5h;	98%
With triethylamine In chloroform at 0 - 20℃; for 2.5h;	98%

: 18370-81-5
(3-bromopropyl)amine

: 4457-32-3
4-nitrobenzyl chloroformate

: 78358-91-5
(3-bromopropyl)-carbamic acid 4-nitrobenzyl ester

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 20℃; for 2h;	98%

: (±)-2-endo-amino-3-exo-isopropylbicyclo[2.2.1]heptane hydrochloride

: 4457-32-3
4-nitrobenzyl chloroformate

: rac-4-nitrobenzyl-(3-exo-isopropylbicyclo[2.2.1]heptan-2-endoyl)carbamate

Conditions

Conditions	Yield
Stage #1: (±)-2-endo-amino-3-exo-isopropylbicyclo[2.2.1]heptane hydrochloride With sodium carbonate In dichloromethane; water at 0 - 20℃; for 0.5h; Stage #2: 4-nitrobenzyl chloroformate In dichloromethane; water at 0 - 20℃; for 16h; Inert atmosphere;	98%

: 85760-58-3
(pivaloyloxy)methyl 6α-<1(R)-hydroxyethyl>penicillanate

: 4457-32-3
4-nitrobenzyl chloroformate

: 124093-83-0
(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>penicillanate

Conditions

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane for 16h; Ambient temperature;	97%

: 93591-35-6
(3S,4R)-4-diethoxyphosphinyl-3-<(R)-1-hydroxyethyl>-1-(4-methoxyphenyl)-2-azetidinone

: 4457-32-3
4-nitrobenzyl chloroformate

: 93591-37-8
(3S,4R)-4-diethoxyphosphinyl-1-(4-methoxyphenyl)-3-<(R)-1-(4-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

Conditions

Conditions	Yield
With dmap In dichloromethane for 2h; Ambient temperature;	97%
With dmap In dichloromethane	79%

: 120476-55-3
N-propyl-6-hydroxyoctylamine

: 4457-32-3
4-nitrobenzyl chloroformate

: 120476-71-3
(6-Hydroxy-octyl)-propyl-carbamic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
With potassium hydroxide In diethyl ether Ambient temperature;	97%

: 39994-75-7
L-threonine methyl ester hydrochloride

: 4457-32-3
4-nitrobenzyl chloroformate

: 219851-78-2
Z(NO2)-Thr-OMe

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3.5h; Acylation;	97%

: 4043-87-2
pipecolic Acid

: 4457-32-3
4-nitrobenzyl chloroformate

: 1-(4-nitrobenzyloxycarbonyl)piperidine-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; Shotten-Baumann reaction;	97%

: 648440-61-3
1,12-bis(imidazolin-2-yl)dodecane

: 4457-32-3
4-nitrobenzyl chloroformate

: 648440-67-9
1,12-bis[N,N'-(4-nitrobenzyloxycarbonyl)imidazolin-2-yl]dodecane

Conditions

Conditions	Yield
With triethylamine In chloroform at 0 - 20℃;	96%

: 21715-90-2
endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide

: 4457-32-3
4-nitrobenzyl chloroformate

: 1154758-31-2
N-(4-nitrobenzyl carbonate)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid imide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 4h;	96%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 6h;	95.1%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h;	87.9%

: N-hydroxy-5-norbornene-2,3-dicarboximide

: 4457-32-3
4-nitrobenzyl chloroformate

: (N-hydroxy-5-norbornene-2,3-dicarboxyl-imido)-4-nitro-benzoate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 4h;	96%

: 1195164-50-1
N-hydroxy-5-norbomene-2,3-dicarboxylic acid imide

: 4457-32-3
4-nitrobenzyl chloroformate

: 1154758-31-2
N-(4-nitrobenzyl carbonate)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid imide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 4h;	96%

: (2S,3S)-S-p-methoxybenzyl-3-methylcysteine allyl ester

: 4457-32-3
4-nitrobenzyl chloroformate

: 1374893-41-0
C23H26N2O7S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 16h; Inert atmosphere;	96%
With N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere;

: 84590-35-2
[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-ylamino]-acetic acid ethyl ester

: 4457-32-3
4-nitrobenzyl chloroformate

: 84590-36-3
[[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-yl]-(4-nitro-benzyloxycarbonyl)-amino]-acetic acid ethyl ester

Conditions

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether; water for 3h; Ambient temperature;	95%

: 287119-91-9
methyl 2-methoxy-5-(N-methylamino)phenylacetate

: 4457-32-3
4-nitrobenzyl chloroformate

: 287119-95-3
methyl 2-methoxy-5-[N-methyl-N-(4-nitrobenzyloxycarbonyl)]aminophenylacetate

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; Acylation;	95%

: 10-triethylsilyl-10-deacetylbaccatin III

: 4457-32-3
4-nitrobenzyl chloroformate

: 7-p-nitrobenzyloxycarbonyl-10-Triethylsilyl-10 desacetylbaccatin III

Conditions

Conditions	Yield
With dmap In chloroform at 20℃; for 0.75h;	95%
With dmap In dichloromethane	94%

: 4457-32-3
4-nitrobenzyl chloroformate

: 496048-68-1
(2S,4R)-2-(4-aminomethylthiazol-2-yl)-4-(tert-butyldimethylsilanyloxy)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

: 496048-70-5
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[4-(p-nitrobenzyloxycarbonylaminomethylthiazol-2-yl)]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h;	94.2%

: 88192-19-2
3-azidopropylamine

: 4457-32-3
4-nitrobenzyl chloroformate

: 4-nitrobenzyl (3-azidopropyl)carbamate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 24h;	94.2%

: 85994-38-3
(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-((R)-1-hydroxy-ethyl)-azetidin-2-one

: 4457-32-3
4-nitrobenzyl chloroformate

: Carbonic acid (R)-1-{(2R,3S)-1-(tert-butyl-dimethyl-silanyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester 3-nitro-benzyl ester

Conditions

Conditions	Yield
With dmap In dichloromethane	94%

4-Nitrobenzyl chloroformate Specification

The IUPAC name of 4-Nitrobenzyl chloroformate is (4-nitrophenyl)methyl carbonochloridate. With the CAS registry number 4457-32-3 and EINECS 224-708-6, it is also named as Carbonochloridic acid, (4-nitrophenyl)methyl ester. The product's categories are Benzene Derivatives; Active Esters / Additives; Coupling; Peptide Synthesis. It is off-white to pale yellow powder which is stable, but moisture-sensitive. Additionally, this chemical should be sealed in the container, avoided direct sunshine and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.42; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.42; (4)ACD/LogD (pH 7.4): 2.42; (5)ACD/BCF (pH 5.5): 40.35; (6)ACD/BCF (pH 7.4): 40.35; (7)ACD/KOC (pH 5.5): 490.96; (8)ACD/KOC (pH 7.4): 490.96; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 72.12 Å²; (13)Index of Refraction: 1.571; (14)Molar Refractivity: 48.97 cm³; (15)Molar Volume: 148.9 cm³; (16)Surface Tension: 53.3 dyne/cm; (17)Enthalpy of Vaporization: 57.34 kJ/mol; (18)Vapour Pressure: 0.000163 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Exact Mass: 214.998535; (21)MonoIsotopic Mass: 214.998535; (22)Topological Polar Surface Area: 72.1; (23)Heavy Atom Count: 14; (24)Complexity: 220.

Preparation of 4-Nitrobenzyl chloroformate: It can be obtained by carbonyl dichloride and (4-nitro-phenyl)-methanol. This reaction needs solvent CH₂Cl₂ at temperature of 20-25 °C. The reaction time is 50 hours. The yield is 98%.

The 4-Nitrobenzyl chloroformate can be obtained by carbonyl dichloride and (4-nitro-phenyl)-methanol

Uses of 4-Nitrobenzyl chloroformate: It can react with trans-4-hydroxy-L-proline to get trans-4-hydroxy-1-(4-nitro-benzyloxycarbonyl)-L-proline. This reaction needs reagent 4 M aq. NaOH at temperature of 0 °C. The reaction time is 3 hours. The yield is 90%.

4-Nitrobenzyl chloroformate can react with trans-4-hydroxy-L-proline to get trans-4-hydroxy-1-(4-nitro-benzyloxycarbonyl)-L-proline

When you are using this chemical, please be cautious about it as the following:
It is not only toxic by inhalation, in contact with skin and if swallowed, but also irritating to eyes and respiratory system. And it can cause burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After using it, take off immediately all contaminated clothing. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of insufficient ventilation, wear suitable respiratory equipment. Besides, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. SMILES:[O-][N+](=O)c1ccc(cc1)COC(Cl)=O
2. InChI:InChI=1/C8H6ClNO4/c9-8(11)14-5-6-1-3-7(4-2-6)10(12)13/h1-4H,5H2
3. InChIKey:MHSGOABISYIYKP-UHFFFAOYAK

Product Name

4-Nitrobenzyl chloroformate

Synthetic route

4-Nitrobenzyl chloroformate Specification

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