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334-99-6

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334-99-6 Usage

Chemical Properties

Midnight blue, fairly stable gas; disagreeable odor. Nonflammable.

Uses

Monomer for nitroso rubber.

Preparation

Trifluoronitrosomethane may be prepared by the reaction of bromotrifluoromethane and nitric oxide in the presence of light and a mercury catalyst:The nitroso compound is also obtained by the pyrolysis of trifluoroacetyl nitrite, which is prepared by reaction of trifluoroacetic anhydride and nitrogen trioxide:

Hazard

Strong irritant to mucous membranes and tissue.

Check Digit Verification of cas no

The CAS Registry Mumber 334-99-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,3 and 4 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 334-99:
(5*3)+(4*3)+(3*4)+(2*9)+(1*9)=66
66 % 10 = 6
So 334-99-6 is a valid CAS Registry Number.
InChI:InChI=1/CF3NO/c2-1(3,4)5-6

334-99-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name trifluoro(nitroso)methane

1.2 Other means of identification

Product number -
Other names Methane, trifluoronitroso-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:334-99-6 SDS

334-99-6Synthetic route

(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
With nitrosylchloride; cesium fluoride In 1,2-dimethoxyethane at -196 - 25℃; for 3h;92%
perfluoro-NN'-dimethylethane-1,2-bis(amino-oxyl) diradical
36525-64-1

perfluoro-NN'-dimethylethane-1,2-bis(amino-oxyl) diradical

A

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

B

perfluoro(4,7-dimethyl-1,3-dioxa-2-tetrafluorothia-4,7-diazacycloheptane)
93638-94-9

perfluoro(4,7-dimethyl-1,3-dioxa-2-tetrafluorothia-4,7-diazacycloheptane)

Conditions
ConditionsYield
With sulfur tetrafluoride at -196℃; for 24h;A n/a
B 87%
bis(trifluoromethyl)cadmium, diglyme adduct

bis(trifluoromethyl)cadmium, diglyme adduct

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
With Trimethylzinn-nitrat monohydrat In acetonitrile Ambient temperature;60%
Perfluoro-2-azapropen
371-71-1

Perfluoro-2-azapropen

A

carbon tetrafluoride
75-73-0

carbon tetrafluoride

B

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

C

perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)
6141-72-6

perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)

Conditions
ConditionsYield
With difluoroether; fluorine; cesium fluoride at -78 - 25℃; for 48h; Addition; Decomposition;A 11%
B 12%
C 77%
Trifluoromethylzinc bromide acstonitrile complex

Trifluoromethylzinc bromide acstonitrile complex

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
With aluminium trichloride; isopropyl nitrate at -15℃;47%
bis(trifluoromethyl)cadmium*glyme

bis(trifluoromethyl)cadmium*glyme

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
With nitrosylchloride98%
bis(trifluoroacetyl)peroxide
383-73-3

bis(trifluoroacetyl)peroxide

A

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

B

bis-trifluoromethyl-aminooxyl
2154-71-4

bis-trifluoromethyl-aminooxyl

Conditions
ConditionsYield
With sodium nitrite In 1,1,2-Trichloro-1,2,2-trifluoroethane at 20℃;
cyanogen chloride
506-77-4

cyanogen chloride

A

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

B

hexafluoroazomethane

hexafluoroazomethane

Conditions
ConditionsYield
With silver(II) fluorideA n/a
B 90%
N,N-bis(trifluoromethyl)hydroxylamine
359-63-7

N,N-bis(trifluoromethyl)hydroxylamine

A

hypofluorous acid trifluoromethyl ester
373-91-1

hypofluorous acid trifluoromethyl ester

B

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

C

difluoramino trifluoromethane
335-01-3

difluoramino trifluoromethane

D

fluoro-bis-trifluoromethyl-amine
359-62-6

fluoro-bis-trifluoromethyl-amine

Conditions
ConditionsYield
With fluorine; cesium fluoride In trichlorofluoromethane at -78℃; for 24h; Fluorination; Further byproducts given;
iodotrifluoromethane
2314-97-8

iodotrifluoromethane

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
With nitric oxide anion In gas at 36.9℃; Rate constant;
With nitrogen(II) oxide Irradiation.im UV-Licht;
With nitrogen(II) oxide under 200 Torr; Irradiation;
perfluoro(2,6-dimethyl-3,5-dioxa-4-thia-2,6-diazaheptane 4,4-dioxide)
21950-98-1

perfluoro(2,6-dimethyl-3,5-dioxa-4-thia-2,6-diazaheptane 4,4-dioxide)

A

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

B

sulphur dioxide

sulphur dioxide

Conditions
ConditionsYield
at 350℃; under 1 Torr;
nitrosyl trifluoroacetate
667-29-8

nitrosyl trifluoroacetate

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
With Perfluorotributylamine; nitrogen(II) oxide Heating;
Heating;
Dichloromethylsilane
75-54-7

Dichloromethylsilane

bis-trifluoromethyl-aminooxyl
2154-71-4

bis-trifluoromethyl-aminooxyl

A

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

B

N,N-bis(trifluoromethyl)hydroxylamine
359-63-7

N,N-bis(trifluoromethyl)hydroxylamine

C

dichloromethylsilane
58310-34-2

dichloromethylsilane

Conditions
ConditionsYield
for 6h; Ambient temperature; in vacuo;A n/a
B 50%
C 85%
tris(trifluoromethyl)arsine
432-02-0

tris(trifluoromethyl)arsine

nitrosylchloride
2696-92-6

nitrosylchloride

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
100°C, 2 h in bomb tube, or warming to 200°C;
With mercury Irradiation (UV/VIS); in presence of Hg;<1
With Hg Irradiation (UV/VIS); in presence of Hg;<1
100°C, 2 h in bomb tube, or warming to 200°C;
iodotrifluoromethane
2314-97-8

iodotrifluoromethane

A

chlorotrifluoromethane
75-72-9

chlorotrifluoromethane

B

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
With nitrogen(II) oxide; chlorine at 22.9℃; under 11.7 Torr; for 0.00833333h; Rate constant; Irradiation; var. of pressure;A 9.17%
B n/a
tris(trifluoromethyl)arsine
432-02-0

tris(trifluoromethyl)arsine

nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
With mercury Irradiation (UV/VIS); 5 d in presence of Hg;4%
With Hg Irradiation (UV/VIS); 5 d in presence of Hg;4%
silver-salt of/the/ trifluoroacetic acid

silver-salt of/the/ trifluoroacetic acid

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
With nitrosylchloride Erhitzen des Reaktionsprodukts;
silver(I) cyanide
506-64-9

silver(I) cyanide

A

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

B

difluoro-carbamic acid-fluoride

difluoro-carbamic acid-fluoride

Conditions
ConditionsYield
With calcium fluoride; fluorine beim vermindertem Druck;
With calcium fluoride; fluorine; potassium nitrate; silver(l) oxide beim vermindertem Druck;
ethanedinitrile
460-19-5

ethanedinitrile

fluorine
7782-41-4

fluorine

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
In neat (no solvent)
In neat (no solvent)
Bromotrifluoromethane
75-63-8

Bromotrifluoromethane

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
With nitric oxide anion In gas at 36.9℃; Rate constant;
tris(trifluoromethyl)arsine
432-02-0

tris(trifluoromethyl)arsine

nitrosylchloride
2696-92-6

nitrosylchloride

A

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

B

arsenic trichloride
7784-34-1

arsenic trichloride

Conditions
ConditionsYield
In neat (no solvent) heating at 100 - 200°C in tube;;
In neat (no solvent) heating at 100 - 200°C in tube;;
trans-chlorotetrafluoro(trifluoromethyl)sulfur(VI)
25030-42-6, 42179-04-4

trans-chlorotetrafluoro(trifluoromethyl)sulfur(VI)

nitrosylchloride
2696-92-6

nitrosylchloride

A

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

B

silicon tetrafluoride
7783-61-1

silicon tetrafluoride

Conditions
ConditionsYield
byproducts: Cl2; Irradiation (UV/VIS); 150°C, 12 h;A 40%
B n/a
byproducts: Cl2; Irradiation (UV/VIS); 150°C, 12 h;A 40%
B n/a
cyanogen chloride
506-77-4

cyanogen chloride

A

cis-hexafluoroazomethane
73513-59-4

cis-hexafluoroazomethane

B

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
With silver(II) fluoride
trifluoroacetyl peroxynitrate
53340-26-4

trifluoroacetyl peroxynitrate

A

Carbonyl fluoride
353-50-4

Carbonyl fluoride

B

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

Conditions
ConditionsYield
With nitrogen(II) oxide at 26.4℃; under 750.06 Torr; Rate constant; Mechanism;
chlorotrifluoromethane
75-72-9

chlorotrifluoromethane

A

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

B

CF2NO

CF2NO

Conditions
ConditionsYield
With nitric oxide anion In gas at 36.9℃; Rate constant;
(trifluoromethyl)phosphonous dichloride
421-58-9

(trifluoromethyl)phosphonous dichloride

nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

A

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

B

(trifluoromethyl)phoshporyl dichloride
51965-64-1

(trifluoromethyl)phoshporyl dichloride

Conditions
ConditionsYield
byproducts: NOCl, N2O, N2; 100°C (72 h); oxydation;A n/a
B 54%
C 13%
iodotrifluoromethane
2314-97-8

iodotrifluoromethane

nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

A

carbon tetrafluoride
75-73-0

carbon tetrafluoride

B

Hexafluoroethane
76-16-4

Hexafluoroethane

C

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

D

trifluoronitromethane
335-02-4

trifluoronitromethane

E

iodine
7553-56-2

iodine

Conditions
ConditionsYield
In neat (no solvent) byproducts: N2, NO2; other Radiation; radiation with γ-rays in the presence of NO as radical trap; mechanism discussed;;
iodotrifluoromethane
2314-97-8

iodotrifluoromethane

nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

A

carbon tetrafluoride
75-73-0

carbon tetrafluoride

B

Carbonyl fluoride
353-50-4

Carbonyl fluoride

C

Hexafluoroethane
76-16-4

Hexafluoroethane

D

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

E

iodine
7553-56-2

iodine

Conditions
ConditionsYield
In neat (no solvent) byproducts: N2, NO2; other Radiation; radiation with γ-rays and NO as radical trap; mechanism discussed; further products;; yields given;;
silver(II) fluoride

silver(II) fluoride

cyanogen chloride
506-77-4

cyanogen chloride

A

cis-hexafluoroazomethane
73513-59-4

cis-hexafluoroazomethane

B

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

tris(trifluoromethyl)arsine
432-02-0

tris(trifluoromethyl)arsine

nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

A

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

B

trifluoronitromethane
335-02-4

trifluoronitromethane

Conditions
ConditionsYield
70°C, 4 d; further unidentified products;
70°C, 4 d; further unidentified products;
trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

cyclohexa-1,3-diene
1165952-91-9

cyclohexa-1,3-diene

3-Trifluoromethyl-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene
75630-26-1

3-Trifluoromethyl-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene

Conditions
ConditionsYield
at 25℃; for 1h;100%
methanesulfonamide
3144-09-0

methanesulfonamide

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

trifluoromethylazosulfonylmethane

trifluoromethylazosulfonylmethane

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 12h;100%
trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

sulfanilamide
63-74-1

sulfanilamide

4-(Trifluoromethyl-azo)-benzenesulfonamide

4-(Trifluoromethyl-azo)-benzenesulfonamide

Conditions
ConditionsYield
In methanol at 20℃; for 24h;100%
trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

benzenesufonyl hydrazide
80-17-1

benzenesufonyl hydrazide

N-trifluoromethyl-N-hydroxybenzenesulfonamide
88978-51-2

N-trifluoromethyl-N-hydroxybenzenesulfonamide

Conditions
ConditionsYield
In tetrahydrofuran for 1.5h; Product distribution; Ambient temperature; oth. arenesulfonohydrazides, oth. solvent,;99%
trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

4-phenyl-semicarbazide
537-47-3

4-phenyl-semicarbazide

C8H7F3N4O

C8H7F3N4O

Conditions
ConditionsYield
In methanol Ambient temperature;98%

334-99-6Relevant articles and documents

Shock-Wave Study of the High-Temperature UV Absorption and the Recombination of CF3 Radicals

Glaenzer, K.,Maier, M.,Troe, J.

, p. 1681 - 1686 (1980)

The high-temperature UV absorption and the recombination of CF3 radicals have been investigated in shock-wave experiments.CF3 radicals were produced near 1300 K in the fast dissociation of (CF3)2N2 and of CF3NO.At pressure of the bath gas Ar between 0.3 and 25 atm, the recombination was found to be in the unimolecular falloff range closer to the high than to the low pressure limit.Extrapolation to the high pressure limit gives krec,infinite(CF3)=(1.9+/-0.9)E13 cm3 mol-1 s-1 at T=1300 K.Earlier low-temperature results are compared with the present data by using unimolecular rate theory.

Jander, J.,Haszeldine, R. N.

, (1954)

On the reaction of perfluoro-aza-propene with oxygen difluoride and fluorination of bis(trifluoromethyl)-hydroxylamine

Minkwitz, Rolf,Reinemann, Stefan,Ludwig, Ralf

, p. 145 - 149 (1999)

The reactions of perfluoro-aza-propene CF3NCF2 with an excess of oxygen difluoride OF2 and the fluorination of bis(trifluoromethyl)-hydroxylamine (CF3)2NOH are discussed. Additionally, we present density functional calculations (B3LYP/6-31G*) on bis(trifluoromethyl)-hypofluorite (CF3)2NOF, which clearly show that this molecule is a model substance for the discussion of negative hyperconjugation.

Kibby,Weston Jun.

, p. 1084 (1968)

Neue Syntheseverfahren fuer Nitrosoperfluoralkane CnF(2n+1)NO (n = 1, 2, 3, 6)

Ludovici, K.,Naumann, D.,Siegemund, G.,Tyrra, W.,Varbelow, H.-G.,Wrubel, H.

, p. 273 - 274 (1995)

Perfluoronitrosomethane, CF3NO, may be isolated in ca. 50percent yield of a reaction mixture of i-C3H7ONO2 with ZnBr(CF3)*2CH3CN in the presence of aluminium trichloride.Approximately quantitative yields of CnF(2n+1)NO (n = 1, 2, 3, 6) may be obtained by reacting NOCl with Cd(CnF(2n+1))2*glyme.The preparations are described. - Keywords: Perfluoronitrosoalkanes; Syntheses; F-Alkylcadmium complexes

DIE REAKTION VON (CF3)2Cd*D MIT (CH3)Sn(ONO2): EIN NEUES DARSTELLUNGSVERFAHREN FUER CF3NO

Lange, Horst,Naumann, Dieter

, p. 93 - 96 (1984)

CF3NO is formed from the reaction of (CH3)3Sn(ONO2) with (CF32Cd*diglyme at room temperature as the only volatile product in 60 percent yield.

-

Dinwoodie,Haszeldine

, p. 1675,1677 (1965)

-

Reactivity of Negative Ions with Trifluoromethyl Halides

Morris, Robert A.,Viggiano, A. A.,Miller, Thomas M.,Seeley, John V.,Arnold, Susan T.,et al.

, p. 10641 - 10645 (2007/10/03)

The kinetics of the reactions of selected anions (A(-)) with the trifluoromethyl halides CF3X (X = F, Cl, Br, I) in the gas phase were measured at 300 K.Reaction rate constants and product branching fractions were determined using a selected ion flow tube (SIFT) instrument.The chosen anions were C5F5N(-), o-, m-, and p-CF3C6H4CN(-), C6F5Br(-), C6F5Cl(-), C6F5CF3(-), C6F5COCH3(-), Fe(-), FeCO(-), SF6(-), SO(-), SO2(-), NO(-), NO2(-), and NO3(-).The reactivity of these systems varies from unreactive to collisional, and a variety of reaction types was found.The results of our present and previous measurements on A(-) + CF3X reactions show that, in cases where nondissociative electron transfer (NDET) is energetically allowed, the total reactivity tends to be high, approaching collisional.This suggests that reactivity in these cases is initiated and controlled by electron transfer from the anion.In addition, association reactions tend to be preempted when NDET is energetically allowed.A few exceptions to these tendencies were found and are discussed.

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