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28920-43-6

28920-43-6

Identification

  • Product Name:9-Fluorenylmethyl chloroformate

  • CAS Number: 28920-43-6

  • EINECS:249-313-6

  • Molecular Weight:258.704

  • Molecular Formula: C15H11ClO2

  • HS Code:2915.90

  • Mol File:28920-43-6.mol

Synonyms:Formicacid, chloro-, fluoren-9-ylmethyl ester (8CI);Fluorene-9-methanol,chloroformate (8CI);(9H-Fluoren-9-ylmethoxy)carbonyl chloride;9H-Fluoren-9-ylmethyl chloroformate;AminoTag;FMOC chloride;FmocCl;Fmoc-Cl;Carbonochloridic acid,9H-fluoren-9-ylmethyl ester;

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC,ToxicT

  • Hazard Codes:C,T

  • Signal Word:Danger

  • Hazard Statement:H314 Causes severe skin burns and eye damage

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:Usbiological
  • Product Description:Fmoc-Cl
  • Packaging:50g
  • Price:$ 395
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TRC
  • Product Description:9-FluorenylmethylChlorocarbonate
  • Packaging:25g
  • Price:$ 275
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TRC
  • Product Description:9-FluorenylmethylChlorocarbonate
  • Packaging:100g
  • Price:$ 640
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:9-Fluorenylmethyl Chloroformate [N-Protecting Agent for Peptides Research] >97.0%(HPLC)(T)
  • Packaging:100g
  • Price:$ 495
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:9-Fluorenylmethyl Chloroformate [N-Protecting Agent for Peptides Research] >97.0%(HPLC)(T)
  • Packaging:25g
  • Price:$ 165
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:9-Fluorenylmethyl Chloroformate [N-Protecting Agent for Peptides Research] >97.0%(HPLC)(T)
  • Packaging:5g
  • Price:$ 49
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:(9H-Fluoren-9-yl)methyl chloroformate
  • Packaging:25 g
  • Price:$ 39
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:(9H-Fluoren-9-yl)methyl chloroformate
  • Packaging:100 g
  • Price:$ 80
  • Delivery:In stock
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  • Manufacture/Brand:Soltec Ventures
  • Product Description:(9-Fluorenylmethyl) chloroformate
  • Packaging:1gm
  • Price:$ 25.2
  • Delivery:In stock
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  • Manufacture/Brand:Soltec Ventures
  • Product Description:(9-Fluorenylmethyl) chloroformate
  • Packaging:5gm
  • Price:$ 119
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Relevant articles and documentsAll total 12 Articles be found

Carpino,Han

, p. 5748 (1970)

Photo-on-Demand Synthesis of Chloroformates with a Chloroform Solution Containing an Alcohol and Its One-Pot Conversion to Carbonates and Carbamates

Liang, Fengying,Suzuki, Yuto,Tsuda, Akihiko,Yanai, Masaki

supporting information, (2020/04/21)

Chloroformates are key reagents for synthesizing carbonates and carbamates. The present study reports a novel photo-on-demand in situ synthesis of chloroformates with a CHCl3 solution containing a primary alkyl alcohol. It further allowed the one-pot synthesis of carbonates and carbamates through subsequent addition of alcohols or amines, respectively.

Versatile Cp*Co(III)(LX) Catalyst System for Selective Intramolecular C-H Amidation Reactions

Chang, Sukbok,Jung, Hoimin,Kim, Dongwook,Lee, Jeonghyo,Lee, Jia,Park, Juhyeon

supporting information, p. 12324 - 12332 (2020/08/06)

Herein, we report the development of a tailored cobalt catalyst system of Cp*Co(III)(LX) toward intramolecular C-H nitrene insertion of azidoformates to afford cyclic carbamates. The cobalt complexes were easy to prepare and bench-stable, thus offering a convenient reaction protocol. The catalytic reactivity was significantly improved by the electronic tuning of the bidentate LX ligands, and the observed regioselectivity was rationalized by the conformational analysis and DFT calculations of the transition states. The superior performance of the newly developed cobalt catalyst system could be broadly applied to both C(sp2)-H and C(sp3)-H carbamation reactions under mild conditions.

PROCESS FOR PRODUCING CHLOROFORMATE COMPOUND

-

Paragraph 0051-0052; 0060-0067, (2019/06/20)

The present invention provides a method for safely producing a large amount of chloroformate compound with high yield. The chloroformate compound can be produced by mixing and reacting a solution of triphosgene, an amine and an alcohol compound in a flow reactor. The chloroformate compound can also be produced by mixing and reacting a solution of triphosgene with a solution comprising an amine and an alcohol compound in a flow reactor. The amine is preferably tributylamine, and preferably used in an amount of 0.8 to 3 equivalents relative to an amount of the alcohol compound.

Safe and Efficient Phosgenation Reactions in a Continuous Flow Reactor

Yasukouchi, Hiroaki,Nishiyama, Akira,Mitsuda, Masaru

supporting information, p. 247 - 251 (2018/02/23)

Phosgene is widely used in organic synthesis owing to its high reactivity, utility, and cost efficiency. However, the use of phosgene in batch processes on the industrial scale is challenging owing to its toxicity. An effective method to minimize reaction volumes and mitigate the safety risks associated with hazardous chemicals is the use of flow reactors. Consequently, we have established a flow reaction system using triphosgene and tributylamine, which affords a homogeneous reaction that avoids clogging issues. In addition, we have demonstrated that this methodology can be applied to a wide variety of phosgene reactions, including the preparation of pharmaceutical intermediates, in good to excellent yields.

Production and cogeneration N [...] succinimide, N '-di-succinimide-based carbon ester method

-

Paragraph 0036-0037, (2017/02/09)

The invention belongs to the field of fine chemical engineering, and particularly relates to a method for producing fluorenylmethoxycarbonylacyl succinimide and coproducing N,N'-disuccinimidocarbonate. The method comprises the following steps: (1) preparation of Fmoc-cl: adding THF (tetrahydrofuran), 9-fluorenylmethanol and an organic amine catalyst into a reaction kettle, cooling to 0-10 DEG C, adding solid phosgene, and completely reacting; (2) preparation of Fmoc-Osu and DSC: adding Hosu, cooling to -5 to +5 DEG C, dropwisely adding a tributyl amine tetrahydrofuran solution, heating to room temperature, and completely reacting; (3) filtering to obtain a DSC crude product; and (4) carrying out mother solution after-treatment to obtain the Fmoc-Osu. A proper amount of 9-fluorenylmethanol is added into the Hosu/solid phosgene/tributyl amine system to quantitatively generate the two products Fmoc-Osu and DSC, wherein the DSC precipitates in the form of crystalline solid, and the Fmoc-Osu and tributyl amine hydrochloride are still dissolved in the tetrahydrofuran solvent; and therefore, the two products can be respectively subjected to filtration, purification and other routine operations to obtain the refined products with the purity of greater than 99%.

Process route upstream and downstream products

Process route

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

9-Fluorenylmethanol
24324-17-2

9-Fluorenylmethanol

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
Conditions Yield
With tributyl-amine; In toluene; at 0 ℃; Reagent/catalyst; Solvent; Temperature;
98%
With pyridine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
With pyridine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
With tributyl-amine; In toluene; at 0 ℃; for 0.0666667h; Temperature; Flow reactor;
98 %Chromat.
With pyridine; In toluene; at 0 - 20 ℃;
phosgene
75-44-5

phosgene

9-Fluorenylmethanol
24324-17-2

9-Fluorenylmethanol

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
Conditions Yield
In dichloromethane;
74%
In dichloromethane;
With pyridine; In diethyl ether; 1.) 1 h, 0 deg C, 2.) 8 h, 25 deg C;
With pyridine; In tetrahydrofuran; at 0 - 6 ℃; for 13.5h; Temperature; Large scale;
Fmoc-OH
115134-37-7

Fmoc-OH

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
Conditions Yield
With thionyl chloride; In N,N-dimethyl-formamide; at 83 ℃; for 2h;
chloroform
67-66-3,8013-54-5

chloroform

9-Fluorenylmethanol
24324-17-2

9-Fluorenylmethanol

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
Conditions Yield
With oxygen; In acetonitrile; at 20 ℃; for 3h; Irradiation;
phosgene
75-44-5

phosgene

F-ether

F-ether

9-Fluorenylmethanol
24324-17-2

9-Fluorenylmethanol

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
Conditions Yield
In tetrahydrofuran; water;
37.9 g (95.8%)
9-Fluorenylmethanol
24324-17-2

9-Fluorenylmethanol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
Conditions Yield
With dmap; In toluene; at 20 ℃; for 24h;
9H-fluorene
86-73-7

9H-fluorene

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 25 percent
2: 74 percent / CH2Cl2
In dichloromethane;
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
Conditions Yield
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

9-Fluorenylmethanol
24324-17-2

9-Fluorenylmethanol

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
Conditions Yield
With tributyl-amine; In toluene; at 0 ℃; Reagent/catalyst; Solvent; Temperature;
98%
With pyridine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
With pyridine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
With tributyl-amine; In toluene; at 0 ℃; for 0.0666667h; Temperature; Flow reactor;
98 %Chromat.
With pyridine; In toluene; at 0 - 20 ℃;
phosgene
75-44-5

phosgene

9-Fluorenylmethanol
24324-17-2

9-Fluorenylmethanol

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
Conditions Yield
In dichloromethane;
74%
In dichloromethane;
With pyridine; In diethyl ether; 1.) 1 h, 0 deg C, 2.) 8 h, 25 deg C;
With pyridine; In tetrahydrofuran; at 0 - 6 ℃; for 13.5h; Temperature; Large scale;

Global suppliers and manufacturers

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  • GL Biochem (Shanghai) Ltd.
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  • Simagchem Corporation
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  • Chemwill Asia Co., Ltd.
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  • Hangzhou Dingyan Chem Co., Ltd
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  • Amadis Chemical Co., Ltd.
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  • Shaanxi BLOOM TECH Co.,Ltd
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  • LIDE PHARMACEUTICALS LIMITED
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