76114-73-3

Basic information

• Product Name: Propargyl butylcarbamate
• Synonyms: PROPARGYL-N-BUTYLCARBAMATE;propargyl butylcarbamate;N-Butyl propargyl carbamate;BUTYL-2-PROPYNYL ESTER CARBAMIC ACID;2-propynyl butylcarbamate;allylene butyl isocyanate;Allylene N-butyl isocyanate;Butyl-2-propynylestercarbamicacid(BIC)
• CAS NO: 76114-73-3
• Molecular Formula: C₈H₁₃NO₂
• Molecular Weight: 155.19
• Product Categories: Pharmaceutical Intermediates
• Mol File: 76114-73-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 233°C
• Flash Point: 95°C
• Appearance: /
• Density: 0.990
• Vapor Pressure: 0.0558mmHg at 25°C
• Refractive Index: 1.452
• Storage Temp.: 2-8°C
• PKA: 12.03±0.46(Predicted)
• CAS DataBase Reference: Propargyl butylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: Propargyl butylcarbamate(76114-73-3)
• EPA Substance Registry System: Propargyl butylcarbamate(76114-73-3)

Safety Data

• Hazardous Substances Data: 76114-73-3(Hazardous Substances Data)

Usage

General Description

Propargyl butylcarbamate is a synthetic chemical compound commonly used as a preservative and antimicrobial agent in a variety of personal care and cosmetic products. It functions by inhibiting the growth of bacteria, yeast, and mold, thereby prolonging the shelf life and maintaining the quality of the products it is used in. Propargyl butylcarbamate is considered safe for use in cosmetics and personal care products in low concentrations, and is regulated by various government agencies for its use in these applications. However, it is important to note that some individuals may be sensitive or allergic to this compound, so it is important to use it in accordance with safety regulations and guidelines.

InChI:InChI=1/C8H13NO2/c1-3-5-6-9-8(10)11-7-4-2/h2H,3,5-7H2,1H3,(H,9,10)

Synthetic route

propargyl chloroformate (35718-08-2) + N-butylamine (109-73-9) → butylcarbamic acid prop-2-ynyl ester (76114-73-3)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane	97%

S-methyl N-butylthiocarbamate (39078-72-3) + propargyl alcohol (107-19-7) → butylcarbamic acid prop-2-ynyl ester (76114-73-3)

Conditions	Yield
With triethylamine In toluene for 12h; Reflux;	94%

N-butylamine (109-73-9) + polymeric N-propargyloxycarbonyl-O-succinimide → butylcarbamic acid prop-2-ynyl ester (76114-73-3)

Conditions	Yield
In dichloromethane at 40℃; for 24h;	76%

1-bromo-butane (109-65-9) + propargyl alcohol (107-19-7) → butylcarbamic acid prop-2-ynyl ester (76114-73-3)

Conditions	Yield
With tetrabutylammomium bromide In acetonitrile	53%

propargyl alcohol (107-19-7) + Methyl N-n-butylthiocarbamate (73330-93-5) → butylcarbamic acid prop-2-ynyl ester (76114-73-3)

Conditions	Yield
Stage #1: Methyl N-n-butylthiocarbamate With pyridine; bis(trichloromethyl) carbonate In dichloromethane at -10℃; Stage #2: propargyl alcohol In dichloromethane at -10 - 30℃; for 14h;	35%

propargyl alcohol (107-19-7) + n-butyl isocyanide (111-36-4) → butylcarbamic acid prop-2-ynyl ester (76114-73-3)

Conditions	Yield
In tetrachloromethane at 70℃; for 3h;

benzyl azide (622-79-7) + butylcarbamic acid prop-2-ynyl ester (76114-73-3) → butyl-carbamic acid 1-benzyl-1H-[1,2,3]triazol-4-ylmethyl ester (1313994-71-6)

Conditions	Yield
With (3-hydroxy-3-phenyl-2-propenedithioate S,S′)bis(triphenylphosphine-P)copper(I) In chloroform at 60℃; for 5h; Reagent/catalyst;	95%
With C19H18N6O*Cu(1+)*I(1-) In dichloromethane at 20℃; for 24h;	93%
With copper(ll) sulfate pentahydrate; D-glucose; sodium tartrate In methanol; water at 20℃; for 24h;	70%
With iron-copper nanoparticles powder In methanol at 20℃; for 12h;	64%
With copper(l) iodide; sodium hydroxide In methanol at 20℃; for 24h;	43%

butylcarbamic acid prop-2-ynyl ester (76114-73-3) → 3-iodo-2-propynyl butyl carbamate (55406-53-6)

Conditions	Yield
Stage #1: butylcarbamic acid prop-2-ynyl ester With sodium hydroxide; sodium hypochlorite; sodium iodide In water at 0 - 40℃; for 1.5h; Stage #2: With acetic acid In water at 40℃; pH=6.9; Stage #3: With sodium hydrogensulfite In water at 25 - 59℃; pH=6.6; Product distribution / selectivity;	93.2%
Stage #1: butylcarbamic acid prop-2-ynyl ester With sodium hydroxide; sodium hypochlorite; potassium iodide In water at 0 - 20℃; for 1.5h; Stage #2: With acetic acid In water pH=6.9; Stage #3: With sodium hydrogensulfite In water at 55 - 59℃; pH=6.6; Product distribution / selectivity;	93.5%
Stage #1: butylcarbamic acid prop-2-ynyl ester With sodium hydroxide; sodium hypochlorite; sodium iodide In water at 0 - 20℃; for 1.5h; Stage #2: With acetic acid In water pH=6.9; Stage #3: With sodium hydrogensulfite In water at 55 - 59℃; pH=6.6; Product distribution / selectivity;	93.2%

4-azido-1,2-dichlorobenzene (66172-16-5) + butylcarbamic acid prop-2-ynyl ester (76114-73-3) → butylcarbamic acid 1-(3,4-dichlorophenyl)-1,2,3-triazol-4-ylmethyl ester (1428739-57-4)

Conditions	Yield
With (3-hydroxy-3-phenyl-2-propenedithioate S,S′)bis(triphenylphosphine-P)copper(I) In chloroform for 10h;	93%

rac-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate (34583-63-6) + butylcarbamic acid prop-2-ynyl ester (76114-73-3) → butylcarbamic acid 1-(tetrahydrofuran-2-ylmethyl)-1H-[1,2,3]triazol-4-ylmethyl ester (1322786-98-0)

Conditions	Yield
Stage #1: rac-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate With sodium azide In water; N,N-dimethyl-formamide at 80℃; for 4h; Stage #2: butylcarbamic acid prop-2-ynyl ester With (3-hydroxy-3-phenyl-2-propenedithioate S,S′)bis(triphenylphosphine-P)copper(I) In methanol; water; N,N-dimethyl-formamide	73%

butylcarbamic acid prop-2-ynyl ester (76114-73-3) → C8H13NO2

Conditions	Yield
With lithium hydroxide In N,N-dimethyl-formamide at 70℃; for 8h;	68%

1,3-diazido 2-propanol (57011-48-0) + butylcarbamic acid prop-2-ynyl ester (76114-73-3) → butyl-carbamic acid (1-[3-(4-(butylcarbamoyloxymethyl)-1,2,3-triazol-1-yl)-2-hydroxypropyl]-1,2,3-triazol-4-yl)methyl ester (1313994-70-5)

Conditions	Yield
With copper(l) iodide; sodium hydroxide In methanol at 20℃; for 24h;	68%

Upstream product

• 35718-08-2 propargyl chloroformate 
• 109-73-9 N-butylamine 
• 109-65-9 1-bromo-butane 
• 107-19-7 propargyl alcohol 
• 39078-72-3 S-methyl N-butylthiocarbamate 
• 111-36-4 n-butyl isocyanide 
• 73330-93-5 Methyl N-n-butylthiocarbamate 

Downstream Products

• 1313994-71-6 butyl-carbamic acid 1-benzyl-1H-[1,2,3]triazol-4-ylmethyl ester 
• 1428739-57-4 butylcarbamic acid 1-(3,4-dichlorophenyl)-1,2,3-triazol-4-ylmethyl ester 
• 55406-53-6 3-iodo-2-propynyl butyl carbamate 

Relevant articles and documents

An easy and efficient one-step procedure for the preparation of alkyl and aryl alkylcarbamates from S-methyl N-alkylthiocarbamates

A general, one-step procedure for the synthesis of alkyl and aryl alkylcarbamates, by the direct reaction of S-methyl N-alkylthiocarbamates with alcohols or phenols in toluene at reflux in the presence of triethylamine, is reported. All the target products were obtained in high yield (15 examples, average yield 94%) and very high purity (>99.2%). The recovery of a co-product of industrial interest, methanethiol, in an amount of one mole for each mole of thiocarbamate, with complete exploitation of the reagent, should also be noted. Georg Thieme Verlag Stuttgart.

Base catalyzed cyclization of N-aryl and N-alkyl-O-propargyl carbamates to 4-alkylidene-2-oxazolidinones

The base catalyzed cyclization of N-aryl and N-alkyl-O-propargyl carbamates is studied in detail. The effect of various bases and solvents on the efficacy of this cyclization reaction is analyzed and a new base-solvent system (LiOH in DMF) for effective cyclization of these carbamates is reported. A number of differentially substituted O-propargyl carbamates were cyclized to the corresponding 2-oxazolidinones under these conditions. The reaction conditions reported here are mild and no side reactions were observed in any of the substrates studied. A propargyl carbonate group was unaffected during the course of the cyclization of the O-propargyl carbamate group. The propargyl carbamates were prepared from the corresponding alkyl or aryl amines and the corresponding propargyl chloroformate, resulting in oxazolidinones diversely substituted at the nitrogen atom. N-Aryl-O-propargyl carbamates cyclized readily to the corresponding oxazolidinones with LiOH in DMF, whereas N-alkyl-O-propargyl carbamates reacted slowly under the same conditions. O-Propargyl carbamates substituted at the 1-position tend to cyclize faster whereas those substituted at 3-position cyclize considerably slower than the unsubstituted carbamates.

New polymer-supported allyloxycarbonyl (Alloc) and propargyloxycarbonyl (Proc) amino-protecting reagents

New polymer-supported reagents, Alloc-P-OSu and Proc-P-OSu, have been prepared from a polymeric N-hydroxysuccinimide (P-HOSu), and used as solid-supported reagents for the allyloxycarbonyl (Alloc) and propargyloxycarbonyl (Proc) protection of the amino group. These new polymeric reagents are safe and stable, the residual P-HOSu generated after the protection reaction can be easily separated by simple filtration and reused.